Triethylamine → HCID 21316842, compound

HRID 263266Notes

Reaction equation

HRID 263266 reaction equation
[NH2:1][CH2:2][C:3]#[N:4].Cl.[C:6]([N:10]=[C:11]=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>O1CCCC1>[C:3]([CH2:2][NH:1][C:11]([NH:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])#[N:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 21316842HCID 21316842, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring mixture of 18.7 g (0.2 mole) aminoacetonitrile·HCl in 300 ml. dry tetrahydrofuran under a nitrogen atmosphere, there is added 20.4 g. (0.2 mole) t-butyl isocyanate (97%), followed by 28 ml. (0.2 mole) triethylamine. The resulting mixture is heated at reflux for five hours, cooled and the tetrahydrofuran removed at reduced pressure. The solid is recrystallized from ethyl acetate to give N-cyanomethyl-N'-(1,1-dimethylethyl)urea, m.p. 128°-32° (Anal. Calcd. for C7H13N3O: C: 54.17, H: 8.44, N: 27.07; Found: C: 53.84, H: 8.33, N: 26.86.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for five hours
  3. temperaturecooled
  4. customthe tetrahydrofuran removed at reduced pressure
  5. customThe solid is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-76782edad13d470882cc07c6c0098dfc
Source dataset
uspto-grants-1979_05
Patent number
US04156738

Reaction notes

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